(20S)-3-benzyloxy-19,26⁽²⁷⁾-dinorchola-1,3,5⁽¹⁰⁾,16,23E-pentaen-25-oic acid methyl ester

Base Information

• Chemical Name: (20S)-3-benzyloxy-19,26⁽²⁷⁾-dinorchola-1,3,5⁽¹⁰⁾,16,23E-pentaen-25-oic acid methyl ester
• CAS No.: 533925-85-8
• Molecular Formula: C₃₂H₃₈O₃
• Molecular Weight: 470.652

Synonyms:(20S)-3-benzyloxy-19,26⁽²⁷⁾-dinorchola-1,3,5⁽¹⁰⁾,16,23E-pentaen-25-oic acid methyl ester

Chemical Property of (20S)-3-benzyloxy-19,26⁽²⁷⁾-dinorchola-1,3,5⁽¹⁰⁾,16,23E-pentaen-25-oic acid methyl ester

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Technology Process of (20S)-3-benzyloxy-19,26⁽²⁷⁾-dinorchola-1,3,5⁽¹⁰⁾,16,23E-pentaen-25-oic acid methyl ester

There total 5 articles about (20S)-3-benzyloxy-19,26⁽²⁷⁾-dinorchola-1,3,5⁽¹⁰⁾,16,23E-pentaen-25-oic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) + (20S)-3-benzyloxy-19,24-dinorchola-1,3,5(10),16-tetraen-23-al (533925-76-7) → (20S)-3-benzyloxy-19,26(27)-dinorchola-1,3,5(10),16,23E-pentaen-25-oic acid methyl ester (533925-85-8)

Guidance literature:

In dichloromethane; at 0 - 20 ℃; for 24h;

DOI:10.1021/ol030031+

Reference yield:

(8R,9S,13S,14S)-3-Benzyloxy-13-methyl-17-vinyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene (213337-06-5) → (20S)-3-benzyloxy-19,26(27)-dinorchola-1,3,5(10),16,23E-pentaen-25-oic acid methyl ester (533925-85-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: {[P(cyclohexyl)3]2RuCl(CO)H}; HBF₄*OEt₂ / benzene; diethyl ether / 0.25 h / 20 °C

1.2: 88 percent / benzene; diethyl ether / 7 h / 75 °C

2.1: tetrahydrofuran / 0 - 20 °C

3.1: 0.30 g / H₂O₂; KOH / H₂O; tetrahydrofuran / 0.5 h / 20 °C

4.1: allylmagnesium bromide / tetrahydrofuran; diethyl ether / 0.25 h / 20 °C

4.2: 70 percent Turnov_. / (azodicarbonyl)dipiperidine / tetrahydrofuran; diethyl ether / 1 h

5.1: 84 percent / CH₂Cl₂ / 24 h / 0 - 20 °C

With tetrafluoroboric acid diethyl ether; potassium hydroxide; Ru(CO)H(Cl)(tri(cyclohexyl)phosphine)₃; dihydrogen peroxide; allylmagnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; benzene;

DOI:10.1021/ol030031+

Reference yield:

17-(1-methyl-2-propenyl)-3-(phenylmethoxy)-estra-1,3,5(10),16-tetraene (533925-83-6) → (20S)-3-benzyloxy-19,26(27)-dinorchola-1,3,5(10),16,23E-pentaen-25-oic acid methyl ester (533925-85-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 0 - 20 °C

2.1: 0.30 g / H₂O₂; KOH / H₂O; tetrahydrofuran / 0.5 h / 20 °C

3.1: allylmagnesium bromide / tetrahydrofuran; diethyl ether / 0.25 h / 20 °C

3.2: 70 percent Turnov_. / (azodicarbonyl)dipiperidine / tetrahydrofuran; diethyl ether / 1 h

4.1: 84 percent / CH₂Cl₂ / 24 h / 0 - 20 °C

With potassium hydroxide; dihydrogen peroxide; allylmagnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1021/ol030031+

upstream raw materials:

methyl (triphenylphosphoranylidene)acetate

(20S)-3-benzyloxy-19,24-dinorchola-1,3,5⁽¹⁰⁾,16-tetraen-23-al

(8R,9S,13S,14S)-3-Benzyloxy-13-methyl-17-vinyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthrene

17-(1-methyl-2-propenyl)-3-(phenylmethoxy)-estra-1,3,5⁽¹⁰⁾,16-tetraene

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